Mono azo dyestuffs



UNITED STATES PATENT OFFICE MONO AZO DYESTUFFS Richard Fleischhauer,Frankfort-on-the-Main- Fechenheim, Germany, assignor to General AnilineWorks, Inc., New York, N. Y., a corporation of Delaware No Drawing.Application November 7, 1935, erial No. 48,672. In Germany November 9,

4 Claims. (01. 260-92) My present invention relates to new mono azo ofthe above formula) cyclohexyl, a methyldyestufis. These dyestufiscorrespond to the cyclohexyl, butyl, isobutyl, amyl, benzyl, phenylgeneral formula: and containing as acyl group, acetyl, propionyl,

\ R4 butyryl, alkoxyacetyl, phenoxyacetyl, w-halogenaoetyl,hexahydrobenzoyl, benzoyl, methoxy- 5 X OH carbonyl C O O C Ha)ethoxycarbonyl 0 00002115) Suitable combining components are forinstance: l-phenoxyacetyl-amino-8-h y d r o x ya \Ynaphthalene-4,6-disulfonic acid, its derivatives 10 l containing in thephenyl radical methyl, ohloro Y or nitro, l-n-butoxyacetylaminoorl-oycloin which formula one X stands for hydrogen andhexyloxyacetylamino- 8 -hydroxy-naphthalene-3, the other for the radicle6- or 4,6-disulfonic acid.

R1 The present new monoazodyestuffs dye fibers,

especially wool or silk, bright scarlet shades of a good fastness tolight, washing and fulling.

Rr'co They may also .be'used for the manufacture of R1 standing for amember of the group consisting c0101. lakes of alkyl containing more 2carbon atoms In order to further illustrate my invention the cycloalkyl,aralkyl and aryl radicles of the benzene following examples are given,the parts being by 'Standmg for a member of the group weight and alltemperatures in oentigrade deconslstmg of alkoxy Cycloalkyl and arylgrees, but it is to be understood, that my invenlgdicles of the g :5 mfga i tion is not limited to the particular products nor 95 3 means memer 0 6 group consls 1 g 0 reacting conditionsmentioned therein.

hydrogen methyl, chlorine and sulfonic acid group, one Y stands forhydrogen and the other Emmple 1 for a sulfonic acid group, R4 stands fora member s of the group consisting of hydrogen and alkyl Parts Of y y cand R5 stands for a member of t group. aminobenzene are diazotized inthe usual manner. sisting of alkyl containing more than 3 carb n Thediazo solution obtained is allowed to flow into atoms,-cycloalkyl andaryl radicles of the benzene a Solution of 44 Parts Of y ce y no- Series8-naphthol-4=,6-disulfonic acid containing an These dyestufis areobtained by diazotizing an EXCESS o Sodium Ca b nateacylamino-arylaminecontaining the aforesaid The isolated dyestuff represents when dry aradicals R1, R2, R3 and combining the diazo comred powder, whichdissolves in water and dyes pound with anl-acylamino-8-hydroxy-naphthawool from an acid bath very clearscarlet-red lene-disulfonic acid containing the aforesaid shades of anexcellent fastness to washing, fulling radicals R4 and R5. and light. Itcorresponds to the formula:

1 1, H: OH NHOOOHrO-O[Hn OHa-OHr-OH: -11 N=N Ha H2 2 I HO; v OH -CO sou:

Suitable diazo components are for instance Similar dyestuffs areobtained by starting from :Ithose' acylamino-arylamines containing assubl-amyloxy- (or cyclohexyloxy)-acetylamino-8- stituent of the acylatedamino group (radical R1 ,naphthol-Afi-disulfonic acid. V V

I so

V benzene, 1-n-butyl-acetylamino-4-amino-2- Example 2 23.2 parts of1-cyclohexyl-acetylamino-4- amino-benzene are diazotized in the usualmanner. The diazo solution obtained is allowed to flow into a solutionof 50 parts of 1(o-chlorophenoxy-acetylamino) -8 naphthol 4,6 disulfonicacid containing an excess of sodium carbonate. After heating the massthe dye-stuff obtained is isolated by filtration. It represents when drya red powder soluble in water and dyes wool and silk bright scarletshades of an excellent fastness to sea-water, fulling, perspiration andlight. It corresponds to the formula:

-3 methylbenzene, 1-propy1-acetylamino-3- aminobenzene,l-benzyl-acetylamino-4-aminobenzene,1-phenyl-acetylamino-i-aminobenzene, 1-amyl-acetylamino-l-aminobenzene,very similar dyestuifs are obtained.

The analogous dyestufi derived froml-cyclohexyl-acetylamino-4-aminobenzene and the same coupling componentyields scarlet shades of a still more yellowish tint.

Instead of l-(2'-chlorphenoxyacetyl-amino)- 8-naphthol-4,6-disulfonicacid, other phenoxyacetylamino 8 naphthol 4,6 disulfonic acids which aresubstituted in the phenyl nucleus, or

m B: on NE-OO-OHr-O H: HOxS OHr-OO so,n

By using instead of the mentioned diazo component the equivalent amountof l-cyclohexylbenzoylamino-4-amino-benzene, or instead of the couplingcomponent the 1(paraor orthoshades become somewhat more yellowish orbluish. methylphenoxy acetylamino) 8 naphthol-4,6- Dyestufis having thesame qualities, but more disulfonic acid, dyestuffs of a more bluishtint and bluish shades, are obtained by using as coupling similarproperties are obtained. components the analogous derivatives of theSimilar dyestuffs, which are likewise distin-1-amino-8-naphthol-3,6-disulfonic acid.

their N-alkyl derivatives, for instance1-(2'-chlorphenoxyacetyl-ethylamino) -8-naphthol 4,6 disulfonic acid,may be employed, whereby the guished by excellent fastness propertiesand I claim: bright shades, are obtained by using the following 1. Themono azo dyestuffs of the general diazo components: formula:

1-p-methylcyclohexyl-acetylamino 4 amino- R benzene1-o-methylcyclohexyl-acetylamino 3 amino- X OH benzene ooom-o-n.

l-cyclohexyl methoxy-acetylamino-4-amino- C benzene I l-cylohexyl,phenoxy acetylamino -4-am1no- Ho's benzene Y1-cyclohexyl-propionylamino-4-aminobenzene Y 1 cyclohexylchloroacetylamino 4 amino benzene 1 cyclohexyl carbetmxyammo 4 amino inwhich formula one X stands for hydrogen and benzene the other for theradicle 1-cyclohexyl-acetylam1no-4-ammobenzene 2- sulfonic acid.

Example 3 R1 20.6 parts of 1-n-butyl-acetylamino-4-aminobenzene arediazotized and the diazo solution ob RPOO/ tained is allowed to run intoa solution of 50 parts of 1-(2'-chlorophenoxy-acetyl-amino)-8-naphthol-4,6-disulfonic acid.

The dyestuif is precipitated by heating the mass and by the addition ofcommon salt. The precipitate is isolated by filtration and representswhen dry a red powder, which dissolves in water and dyes wool and silkbright scarlet shades, of a very good fastness to Washing, fulling andlight. The dyestuff corresponds to the formula:

R1 standing for a member of the group consisting of alkyl containingmore than 2 carbon atoms, cycloalkyl, aralkyl and aryl radicles of thehenzene series, R2 standing for a member of the group consisting ofalkyl, alkoxy, cycloalkyl and aryl radicles of the benzene series, inwhich formula R3 means a member of the group consisting of OH NH-OO-OHrOom-om-om-on Q om-oo SOzH By using 1-isobuty1-acety1amino-4-aminohydrogenmethyl, chlorine and sulfonic acid (or group, one 5! stands for hydrogenand the other 2,078,470 3 for a sulfonic acid group, R4 stands for amember 3. The mono azo dyestuff of the formula:

11, Hz H Na-oo-om-oOom of the group consisting of hydrogen and alkylwhich dyestufi represents a. red powder soluble and Rs stands for amember of the group eonin water dyeing wool and silk bright red shadessisting of alkyl containing more than 3 carbon of a very good fastnessto sea water, fulling, peratoms, cycloalkyl and aryl radlcles of thebenzene spiration and light.

series, which dyestuffs dye the fibers scarlet 4. The monoazo dyestufiof the formula:

0H NH-CO-CHs-O- CHg-OHrCHa-CHK OHr-CO shades of a good iastness tolight, washing and which dyestuff represents a red powder soluble infulling. water dyeing wool and silk bright scarlet shades 2. The monoazo dyestufi of the formula:

GHr-CO S 0 H which dyestufi represents a red powder soluble in of a,very good fastness to washing, fulling and water dyeing wool and silkbright scarlet shades light. I

of a very good fastness to sea water, fulling, per- RICHARDFLEISCHHAUER. spiration and light.

